Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.2363 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2
InChI
InChIKey=IYRMWMYZSQPJKC-UHFFFAOYSA-N
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.2363 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2094255 |
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Target ID: CHEMBL2345 |
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Target ID: CHEMBL4237 |
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Target ID: CHEMBL1951 |
0.7 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.46 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.84 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1.43 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640 |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.51 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
7.17 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
17.72 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640 |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.47 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
250 mg/kg single, oral dose: 250 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
3.45 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27749255 |
25 mg/kg single, intravenous dose: 25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED |
|
5.11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/26051640 |
6 mg/kg single, oral dose: 6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
KAEMPFEROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
|
| Induction of glutathione synthesis in human keratinocytes by Ginkgo biloba extract (EGb761). | 2001 |
|
| Electrochemical behaviors of quercetin and kaempferol in neutral buffer solution. | 2001 Aug |
|
| Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat. | 2001 Aug |
|
| Four new isoflavone triglycosides from Sophora japonica. | 2001 Aug |
|
| Medicinal foodstuffs. XXV. Hepatoprotective principle and structures of ionone glucoside, phenethyl glycoside, and flavonol oligoglycosides from young seedpods of garden peas, Pisum sativum L. | 2001 Aug |
|
| Effect of processing and storage on the antioxidant ellagic acid derivatives and flavonoids of red raspberry (Rubus idaeus) jams. | 2001 Aug |
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| Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids. | 2001 Aug |
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| Inhibitory activity for chitin synthase II from Saccharomyces cerevisiae by tannins and related compounds. | 2001 Aug |
|
| Ethyl m-digallate from red maple, Acer rubrum L., as the major resistance factor to forest tent caterpillar, Malacosoma disstria Hbn. | 2001 Dec |
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| Proposed active constituents of Dipladenia martiana. | 2001 Dec |
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| Coumaroyl flavonol glycosides from the leaves of Ginkgo biloba. | 2001 Dec |
|
| A new C-methylated flavonoid glycoside from Pinus densiflora. | 2001 Dec |
|
| Inhibition of nitric oxide synthase expression by a methanolic extract of Crescentia alata and its derived flavonols. | 2001 Dec 21 |
|
| Flavonoids as cycline-dependent kinase inhibitors: inhibition of cdc 25 phosphatase activity by flavonoids belonging to the quercetin and kaempferol series. | 2001 Jul |
|
| Specific flavonoids induced nod gene expression and pre-activated nod genes of Rhizobium leguminosarum increased pea (Pisum sativum L.) and lentil (Lens culinaris L.) nodulation in controlled growth chamber environments. | 2001 Jul |
|
| Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L. | 2001 Jul-Aug |
|
| Isolation and antioxidant activity of galloyl flavonol glycosides from the seashore plant, Pemphis acidula. | 2001 Jun |
|
| Flavonoid compounds in the flowers of Kitaibelia vitifolia Willd. (Malvaceae). | 2001 Mar-Apr |
|
| Flavonoids and urate antioxidant interplay in plasma oxidative stress. | 2001 May |
|
| Kaempferol and its glycosides in the seeds hair of Asclepias syriaca L. | 2001 May-Jun |
|
| In vitro anti-inflammatory effects of quercetin 3-O-methyl ether and other constituents from Rhamnus species. | 2001 Nov |
|
| A stabilized flavonoid glycoside in heat-treated Cassia alata leaves and its structural elucidation. | 2001 Nov |
|
| Effects of flavonols on the generation of superoxide anion radicals by xanthine oxidase and stimulated neutrophils. | 2001 Nov 1 |
|
| Direct extraction of specific pharmacophoric flavonoids from gingko leaves using a molecularly imprinted polymer for quercetin. | 2001 Nov 16 |
|
| Phytochemical and pharmacological analysis of Bauhinia microstachya (Raddi) Macbr. (Leguminosae). | 2001 Nov-Dec |
|
| Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation. | 2001 Oct |
|
| Antioxidative components from the aerial parts of Lactuca scariola L. | 2001 Oct |
|
| Indolopyridoquinazoline alkaloid from Leptothyrsa sprucei. | 2001 Oct |
|
| Flavonol glycosides from the stems of Trigonella foenum-graecum. | 2001 Oct |
|
| Determination of flavonoids and stilbenes in red wine and related biological products by HPLC and HPLC-ESI-MS-MS. | 2001 Sep |
|
| Polyphenolic compounds: interactions with the gut and implications for human health. | 2001 Sep |
|
| Antipruritic and antidermatitic effect of extract and compounds of Impatiens balsamina L. in atopic dermatitis model NC mice. | 2001 Sep |
|
| Antimicrobial activity of Argentine plants used in the treatment of infectious diseases. Isolation of active compounds from Sebastiania brasiliensis. | 2001 Sep |
|
| Flavonoids protect neurons from oxidized low-density-lipoprotein-induced apoptosis involving c-Jun N-terminal kinase (JNK), c-Jun and caspase-3. | 2001 Sep 15 |
|
| Qualitative and quantitative chromatographic investigation of flavonoids in Bellis perennis L. | 2001 Sep-Oct |
|
| Flavonoids from the flowers of Prunus spinosa L. | 2001 Sep-Oct |
|
| Flavonoids and UV photoprotection in Arabidopsis mutants. | 2001 Sep-Oct |
|
| Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). | 2002 Apr 10 |
|
| Phenolic compounds and antioxidant capacity of Georgia-grown blueberries and blackberries. | 2002 Apr 10 |
|
| The role of UV-B radiation in aquatic and terrestrial ecosystems--an experimental and functional analysis of the evolution of UV-absorbing compounds. | 2002 Feb |
|
| Oxidation of the flavonoids galangin and kaempferide by human liver microsomes and CYP1A1, CYP1A2, and CYP2C9. | 2002 Feb |
|
| Flavonoid gene expression and UV photoprotection in transgenic and mutant Petunia leaves. | 2002 Jan |
|
| A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
|
| Isolation and characterization of stelladerol, a new antioxidant naphthalene glycoside, and other antioxidant glycosides from edible daylily (hemerocallis) flowers. | 2002 Jan 2 |
|
| Antioxidant activity of flavonoids from Licania licaniaeflora. | 2002 Mar |
|
| Hepatoprotective principles from the flowers of Tilia argentea (linden): structure requirements of tiliroside and mechanisms of action. | 2002 Mar |
|
| Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. | 2002 Mar 1 |
|
| Structure-activity relationships for inhibition of human 5alpha-reductases by polyphenols. | 2002 Mar 15 |
|
| Selective responses of three Ginkgo biloba leaf-derived constituents on human intestinal bacteria. | 2002 Mar 27 |
Patents
Sample Use Guides
humans: orally as a component of plant (e.g. Elaeagnus Angustifolia or Ginkgo Biloba) extracts.
mice: 100 mg/kg/d, p. o. for 6 weeks.
rats: 20 mg/kg; i.p. daily for a period of 28 days.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 22:27:23 UTC 2022
by
admin
on
Fri Dec 16 22:27:23 UTC 2022
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| Record UNII |
731P2LE49E
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| Record Status |
Validated (UNII)
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| Record Version |
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1221 (Number of products:6)
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| Code System | Code | Type | Description | ||
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KAEMPFEROL
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DTXSID7020768
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C68457
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731P2LE49E
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5280863
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7703
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208-287-6
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DB01852
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M6592
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1354900
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C006552
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The compound was screened for it's antioxidant capacity in the DPPH assay, and displayed a high antioxidant activity, with an IC50 value of 89.7 uM.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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